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Rustic Secluded Cabin near Berkshires. *wood stove

The Red House offers a peaceful secluded retreat, surrounded by acres of forest & with excellent hiking trails. Enjoy the tranquility of nature while being minutes from antiquing, Kripalu, the Norman Rockwell Museum, The Mount, Tanglewood, skiing, & Shakespeare & Co. You'll appreciate the serene privacy, situated on an old dirt road. Relax by the wood stove or in the sunroom. Nearby towns of Spencertown, Chatham, & West Stockbridge offer unique charm. 4WD vehicle is recommended for winter visits

Nordic Cabin - Light-Filled & Spacious with Firepi

Nordic Cabin is a mid-century, Scandinavian-inspired home on 6 acres of woods—just 2 hrs from NYC! Bright, light-filled spaces welcome you to unwind. The downstairs open plan design offers a spacious living room with a woodburning stove, a modern kitchen, dining table and a full bath. Upstairs, 3 bedrooms, a full bath, and a rec room with foosball. Outside, enjoy year-round beauty, dine under the stars, stay warm by the firepit, walk meandering trails or explore the nearby historic train line.

Romantic-Private-Western Tiny Cabin w/HOT TUB

Sept. SPECIAL (Mon-Thurs): Prosecco/s’mores kit/firepit supplies. Just 2.5 hours from NYC, escape to The Hitching Post—a romantic Western-inspired tiny home in Chatham, NY w/private hot tub, firepit, outdoor shower & rustic luxury throughout. Once the hideout of a legendary samurai cowboy, this unique retreat features a cozy queen bed nook, luxe bath & kitchenette. Just a 2-minute walk to Chatham’s restaurants, shops, brewery & theater. A perfect Hudson Valley getaway for couples. @artparkhomes

Walk to Main Chatham Villg Fully stocked Priv Park

WELCOME ALL. Pedestrian/Bike friendly Village home 200' to Main St pubs pizza Crandall, Yianni's, Bimi's fine & fun dining. PS21/McHaydn live theaters, shopping. Town park w/swim pond, free tennis courts w/in a mile. 12mi Hudson Amtrak (taxi, Uber avail). ArtOmi, Hawthorne Valley, Tanglewood near. Keyless entry. 100% smoke/pet-free property. Check-in 4pm/-out 11am. 2 laundromats w/in 1/2 mile. High-speed wifi & parking at door. Stocked home. Private outdoor dining w/propane bbq. 2 guests max.

The Cottage on Sylvester Street

The Cottage on Sylvester Street welcomes guests looking for a relaxing weekend or longer stay in a small-village setting. Located at the heart of the historic Village of Kinderhook, this stylishly renovated house is located amongst Kinderhook's collection of historic architectural gems. Within easy walking distance are eateries, wine and beer bars, The School I Jack Shainman Gallery, historic sites, the farmers' market plus farm stands, and quiet, scenic roads perfect for walking and cycling.

Boutique Apt 1-BR in Historic Chatham Landmark

Enjoy a boutique style one-bedroom unit with 5 star reviews & the convenience of a charming, full-service restaurant just one flight down. The space is located in the historic 'Chatham House', once a resort for artists & tourists of the Catskill Mountains. While the space and ease of a cozy tavern just downstairs may incur some lazy, the quaint Main St. of Chatham just steps away will have you venturing out to explore the shopping, Pubs and even a movie. A quick 20 min drive to Hudson Amtrak.

Kinderhaus Loft in Chatham, NY

Kinderhaus Loft is on the 3rd floor accessed via an exterior stair case with a deck where you can enjoy views of the gardens & stars. There are lounge chairs and a grill for you to enjoy. The loft is in the center of the Village. You can walk to restaurants, shops, & the Crandall Theatre. You are within a mile of PS21 and MacHaydn Theater. You can also explore Hudson 12 miles away, Kinderhook 6 miles away & the Berkshires are 20-30 miles away. Close to hiking, skiing, theater & the arts.

Luxury Barn Retreat Near Hudson & the Berkshires

Set on eight private acres where New York meets the Berkshires, this architect-designed retreat combines dramatic contemporary design with warmth and comfort. Soaring ceilings, a chef’s kitchen, designer interiors, peaceful outdoor spaces and nearby lake access create the perfect escape. Ideal for couples, families with children or close friends, it’s a short drive from Hudson, Chatham, Great Barrington, Tanglewood and countless other destinations for shopping, dining, hiking and more.

Guest Suite in Old Chatham Hunt Country

Looking for all the perks of a hotel while staying at a house in the country? This tranquil, light filled room overlooks horse pastures and a dirt road in the heart of Old Chatham hunt country. A private entrance leads to a guest suite which includes a queen size bed, sitting area, kitchenette, and walk-in closet. Located on the first floor of a newly built, net-zero home. Power comes from solar and solar water panels provide for guilt-free hot showers! 50 MBPS fiber optic Internet!

Chic Hudson Farmhouse w/ Fireplace & Porch

1873 Stylish & cozy Hudson Farmhouse w/ a wood burning stove & the perfect porch. 14 minute drive to Warren St This 3 bedroom + office home has been lovingly updated while maintaining the original details of this historic property. Located on over an acre of land, on a quiet street, this peaceful retreat is the perfect escape to unwind and relax. With high ceilings, tons of oversized windows, and an open layout, this house feels both airy & bright.

Modern Barn on 12 acres w Sauna, FirePit+swimming

Escape to our recently renovated guest house on a 12-acre property, 15min from Hudson. Take in the rural setting through oversized glass doors. Infared Sauna is within running distance of the swimming pond for a cold plunge. Located in a park like setting of rolling hills & colorful sugar maple trees. Fully equipped kitchen, memory foam mattress and all the amenities. In home Massage/Yoga available. XC ski from the house! 45min to downhill.

Peaceful Tiny House Escape by Hudson & Berkshires

Welcome to "The Tiny" at The Hemptons in the Hudson Valley. The not-so-tiny house is 400sf with plenty of space to stretch out. Each of the two bedroom lofts have a comfy queen bed on a low profile frame. The kitchen is equipped for basic cooking (read: Not good for Thanksgiving, but perfectly suited for standard cooking endeavors). Regretfully, we are unable to accommodate service animals due to the health risk it poses it the owners.